What is the most useful pair of boots you can own? Well, that depends on whether you're a skirts or trousers woman. And the outfit profiling doesn't end there. Short or long skirts? Flared or narrow? Drainpipe trousers or 7/8th length?

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For the past few years, the most popular boot has been one that ends somewhere around the ankle. Who'd have thought? It's not an easy style to get right: wear one that's slightly too high up the ankle and it shortens the leg. Choose one that's too far below the ankle - the infamous shoe-boot - and it can look plain ugly.

Yet just about every woman I know, all of them rational people who would never have considered an ankle boot a decade ago, now wonder how they ever managed without them. Truly the eye is a wondrous organ, so agile in adapting to a leg that's sliced at the knee by a hemline, and again at the ankle by a boot-top. After a while, the brain no longer finds itself thinking, "Ooofff, that's a short, stocky, potato-field leg", and thinks instead, "My, that's a fashionable, Harvey Nichols sort of leg".

But now the fashionable Harvey Nicks leg is being challenged by knee-length boots, which are mounting a big comeback. The advantages of knee-length over ankle-length are obvious: warmth and coverage. Weighed against the plusses though, is the problem of how to wear trousers with them. Tucked in? That just about works if the trousers are skinny and you're happy with a casual weekend vibe, but it's hopeless with pleat-fronted trousers.

And what about tights? Many women find boots and tights suffocating, and don't appreciate the way boots wreck their Wolfords. The most comfortable solution - unless the temperatures are Siberian - is to abandon tights and skimpy underwear in favour of warm socks (Toast's organic wool Fair Isle socks, £25, fit the bill nicely, toast.co.uk) and something like M&S's Secret Slimming, Light Control lingerie shorts, £6, marksandspencer.com. Assuming you're not Rihanna, these are to wear under your skirt or dress, not on their own.

The challenge doesn't end there, I'm afraid. If you're a habitual skinny jeans, short skirt or midi/maxi wearer, the most versatile boots are bikers - a mid-calf that works well with all these looks and helps take a floaty chiffon dress from summer to winter, as well as making it look more youthful. Opt for tractor soles, not just because they're authentic and surprisingly flattering (Armstrong's rule: the chunkier the footwear, the more streamlined, by comparison, the leg) but because they'll stop you breaking your neck come not-enough-salt-or-grit time.

As far as pencil skirts go, knee-highs are a challenge. You'll need an ultra-streamlined cut. I'm not a huge fan of over-the-knee boots, but if you're going for the femme-fatale-with-a-side-of dominatrix, Roland Mouret for Robert Clergerie's skinny leather tall boots are about as good as it gets.

Whatever style you select, avoid tight sausage shapes in stretch fabrics, which look hideous on everyone. Ideally - apart from the aforementioned pencil skirt scenario - knee‑highs should appear snug-fitting round the ankles and slightly loose at the top - it helps to create the impression of dainty legs.

Cue hollow laughter from women who have problems finding boots that fit over their calves, let alone ones that look too loose. That's more women than you'd think incidentally, so why do so many shops exclusively stock narrow cuts? Surely they could triple their sales if, like duoboots.com (which offers up to 21 calf sizes), they offered a choice. You could try moving up a size to see if that makes a difference to the width - a boot's not going to fall off if it's half a centimetre too big. Alternatively, opt for lace-up boots that you can adjust yourself (Jimmy Choo's 10cm high, embroidered black suede lace-ups at jimmychoo.com are the most glamorous incarnations of this genre £1,225; Timberland's Bethel buckle mid-lace-ups, in black and occasionally brown, the most practical, £130, timberlandonline.co.uk and Penelope Chilvers soft, stretchy sheepskin and chocolate leather reversed shearling boot, £462 the most stylishly cosy, penelopechilvers.com).

Ultimately, the weather will decide whether knee-highs win over ankle boots this year. Whatever the outcome - and now we've got the US elections out of the way, isn't this contest exciting? - let's make this the year we leave Uggs where they were originally designed for: granny's chilly bedroom.
Lisa Armstrong

Ladylike midi + biker boots
Bit of a Sam and Aaron Taylor-Johnson situation going on here: it shouldn't work, but it does. The unexpected pairing of hard-edged biker boots with prim midi-dress gives the outfit attitude and a more youthful vibe than if teamed with court shoes. It's basically the sleeker take on the flippy-tea-dress-and-casual-boots combo sported by leggy teens on the summer festival circuit. Actually, biker boots are great for wintrifying your summer wardrobe: try them with white jeans (very Emmanuelle Alt) and shorts (worn with thick woolly tights). Black is best when it comes to biker (brown is a smidgen too workman's boots), and those decked with tough hardware are doing a particularly hot trade at Matches this season: Balenciaga's cut-out clunky gold-buckled ones and Chloé's studded Susannas have both sold out. Footnote: jeans tucked into biker boots still look cool.
Phong Luu

7/8 trousers + ankle boots
Cropped trousers are a match made in ankle-boot heaven, not least because they remove the "to tuck or not to tuck?" headache. That's one problem solved. The other? Finding the optimal ankle-boot height. We say it should be a centimetre or two above the ankle, based on the theory that where the heel starts to incline - aka where the leg is at its slimmest - is where the boot will be most flattering. On this note, Acne's Pistol boots score highly with us - almost everyone on the fashion team owns a pair (or a high-street variant) and we can confirm that, even for those with cankles, they work wonderfully.
PL

Pencil skirt + thigh-high boots
The French have a special name for thigh-high boots -
cuissardes
. The English do, too: hooker boots. Sounds much better in French, doesn't it? The thigh-high still has the lady-of-the-night, unwearable-in-the-day reputation (thanks, Pretty Woman), but we happen to think it looks classy and demure. Yes, demure. Of course, this depends on what you team it with. We'll skip the diktat from the School of the Bleedin' Obvious about miniskirts and skimpy tops, and jump to the what-it-works-with part. And what it works with are great basics: see how the long pencil skirt and knit rein in the sauciness? That's what you're aiming for with the thigh-high. A chunky sweater dress or loose silk shirt-dress will also look great with them (the slim bottom/voluminous top is the golden ratio here). When hunting out your
cuissardes
, look for a pair that's matte black (easier to wear and more flattering; glossy black just looks cheap and nasty) and with a heel; flat ones tend to make you look like a wally in waders. A chunky, Seventies-ish heel will look less dominatrixy than a stiletto one.
PL

Miniskirt + knee-high boots
The big boots story this winter is the return of the knee-high. But instead of tucking them into jeans, try them teamed with a miniskirt - far fresher. Plus, the Sixties-ish vibe is on-the-money for next season. Go for a pair that is slightly loose up top - skintight can make your legs look sausage-like and, anyway, has anyone ever found a pair that fits perfectly around the calf with being baggy at the ankles? Thought not. As with thigh-high boots, consider your proportions carefully: showing a hint of skin between skirt and boots has a slimming effect, and you don't want anything too tight up top with a revealing bottom.
PL